New acid dyestuffs of the anthraquinone series



V -presenc eiflof.Water- Pan I such-n, as SOdlllIl'l carbonatew 017 SQdlllIlT blcar- .partsof meta-aminobenzamide, 2parts of Q wherein R stands' for lyacting snbs't'ance, s uehfals; cupi ous ehlei'ide, ceppe su lfa ite or-thelike 2 I The; new dyestuffs are'ldistinguished-i by clear 'tint and good h They dye the animal fiber from an heid bath Patented, "Feb; 28, 19332 KARLHZAHN mini x0011; or mwnbmbilem mm o61m;

mzwYoRx, N. Y.; ACORPORATION OEDEL'AWARE NEW? DVYEVSV'IUFFS er I ran ANTHRA'Q'UINONE SERIES;

1 No Drawing. Applic'liition 416a Ibrnafy}, 1932, Sena 111%. 590,783, and in;eemany h flnili931.

The 1gresent invention relates to new acid dyestu s of the ant-h 'aquinone series, more, particularly it relates to new 'cd'mpennds: of the generaIfOI'muIa:

turetis maintained until the formation of the dyestufl 1s finished, The dyestufi isisaltfed out by purified by repeatedly redissolving it in water and .-againsalted out. The product obtained for ms ablue'p0wdei' which dyes wool from an 'acidubth clear blue tints of good 1 fastness-propertiesv The dyestuff has the following structural; formula:

X f h da redieehgf iillle benzene serles, or y no enfa yroxy-i a l 1 or cyclohexyl and ie for hydrogen; 1 or and X represent alkyl radicals. Our newdyestufi'sereobtainable by cans t V r ing 1 amino-lhalogen-anthrequinone-2 su1- H n -ec orta ltgt er of to re c w th leoinfihnndbf thegene el' fermlili" I (2) 10 parts of the sodium salt of l-aminm 4-bromo-anthraq I parts of para-aminobenzarnide,v 5 parts of po- -Wherein'R, X- andX- are -identified as abeve =1 1;The:condensati0nfithe] saidcomponents is preferably effected byheatingtthemfin the y v n I acid; binding fag t ride are heated 1n 80 parts of n water at 80 C.-

scribed in Example 1.. It dyes W001 from an acid bath Violet-blue tints" t the; following formula benate, and a :s mall.fqua,ntity ef-e eatalytical- -fastne'sis; properties; u

v The "following examplesgserve, to illustrate the inventibn,';butjthey ai e' not intend-. edv to limit it theneto; the parts" being by Weight:

1) parts of sed-iuniisaltof -1 -amin0-4--. bromo-anthraquin0ne2-su1f0nie acid; 5.5

sodium carbon-ate, 0.5 parts ofeuprouschlm ride are slowly heated in partse f. Miter to 3 Lamina-3e io gs nzamide or Lamina-4} It 909 C. The .dyestufifis' worked up as def and corresponds "m v W t mkthfist Y or; 'JLEVERKUSEN-I; e; wEnx, GERM NY, AssIGNQRsj 1 170 GE ERA C..80" C.,whi1estirring. Theftem peiw.

means of SOdililIl chloride and tassium1carb0nate,"0.5 pait of cuprous chlon its (3) 10 parts of the sodium salt of l-aminoi-bromo-anthraquinone-Q-sulfonic acid, 6 parts of meta-aminobenzoic acid cyclohexylamide, 2 parts of sodium carbonate, 0.5 part of cuprous chloride waterand 20 parts of methyl alcohol at 90 C.100 C. The dyestufli' is isolated and puri fied; it forms a blue powder and dyes wool a l Ithas'the l from an acid bath clear blue tints. following formula V 0 mar II may be amino-benzoic acid cyclohexylamide or ortho-amino-benzoic acid cyclohexylamide.

(4) 10 parts of the sodium salt of 1-amino-a bromo-anthraquinone-2 sulfonic acid are heated w1th6 parts of meta-amino- 2 parts of sodibenzoic acid dimethylamide, um carbonate, 0.5 part-of cuprous chloride and parts of water for 8 hours at C.- 7 0 (3., while "stirring; The dyestufi' precipitates in the form of blue crystals and is purified. by solution and redissolving. It; dyes, wool from an acid bath reddishblue tmts. It has the following formula: A

Instead of meta-amino-benzoic acid dione may also use the chloromethylamide, substitution products of the said compound, for instance, 1-amino-3-chloro 5 benzoic acid dimethylamide or l-amino--chloro-fi-ben I zoic acid dimethylamide. V V

(5) By substituting in Example (4) 6 parts of para-amindbenzoic acid methylamare heated in [80- parts of Thedyestufi' dyes wool ing formula used in an analogous manner parawashing with sodium chloride acid dimethylamide, a blue dyestufi is obtained which has the following formula:

1 $11.. clear blue tints.

(6) By replacing in Example (4) the '6 parts of meta-amino-benzoic acid dimethylamide by 7 arts of meta-amino-benzoic acid ethanolami e (melting at 104 O.105 C.) and by heating for 5 hours at 60 C.7 0 0., a dyestufi is obtained which has the follow- (beam-canon Thedye stufi is separated'from the reaction mixture by salting out; it forms in the dry state a blue powder and dyes wool blue tints of good fastness properties.

Instead of meta-amino-benzoic acid ethanolamide, there may also be used the orthoor para-compound of the said amide.

(7.) 10parts of the sodium salt of Lamino- 4=-bromo-anthraquinone-2-su1fonic acid are heated for severalhours a-t'70 (1.45 C. with 6 parts of ortho-aminobenzamide, 2 parts of sodium carbonate, 2 parts-of sodium bicarbonate, 0.5 part of cuprous chloride and 7 0 partsfof water. The dyestuif separates in the form of crystals having a bronze-like luster. Itdyes wool from an acid bath clear bluetints. Itloorresponds to the following formula v O NH:

ide for the 6 parts of meta-amino-benzoic 1. 1:

Dyestuffs having properties similar to those of 'the ,dyestufi's described in the before-mentioned examples are obtained by using components which are analogous to those disclosed in the'speeific examples, such 7 as 0rtho-, metaand para-amino-benzoic a acid monoand diethylamides or nuclear substitution products thereof, as for.instance,- the chloro-substitution products thereof.

tints of goodfastness properties and corresponding to the formula: I r I v V V 0 NHI e claim: v I Y Y 1. As new products,acid'dyestufis dyeing animal fiber from an 'acid bath blue tints and O 0N corresponding to the general formula:

' and X represent alkyl radicals.

"animal fiber p 7 corresponding to the general formula} V 5 ing animallfiber from an acid bath clearblue wherein R stands for a radical of the benzene series, X for hydrogen, alkyl, hydroxyalkyl or ,cycl'ohexyl and X for'hydrogemt or X 7 w AS new products}, ye i I V7 p 7 nf r f gmoli from an acid bathblue tlntsand In jotestimon whereof,"weaflix our signa- I KARL ZAHN; I

o HEINRICH KOCH. V

KLAUS or m; I

wherein X, stands for hydrogen, alkyl, hydroxyalkyl or cyclohexyl and X -f0r hydrogen, orX' and X representalkyl, radicals, and the Ys mean hydrogen orone Yfchlorine.

3. Asa new product, the acid'dyestufi dyea ing animal fiber froman acidfbath clear blue tints of good fastness properties and'corre V 'spondingto the-formulazTt', f o

4. Asa new product, theacid dyestufl dye ing animal fiber from anacid bath clear'blue i 5". As a new product,fthe acid dyestufidye a tintsof good fastne'ss properties and c0rresponding to the formula: r o 5 NH: 

